DE69800882T2 - Benzimidazol-, Benzoxazol-, und Benzothiazolderivate, Verfahren zu ihrer Herstellung und pharmazeutische Zusammensetzungen die sie enthalten - Google Patents
Benzimidazol-, Benzoxazol-, und Benzothiazolderivate, Verfahren zu ihrer Herstellung und pharmazeutische Zusammensetzungen die sie enthaltenInfo
- Publication number
- DE69800882T2 DE69800882T2 DE69800882T DE69800882T DE69800882T2 DE 69800882 T2 DE69800882 T2 DE 69800882T2 DE 69800882 T DE69800882 T DE 69800882T DE 69800882 T DE69800882 T DE 69800882T DE 69800882 T2 DE69800882 T2 DE 69800882T2
- Authority
- DE
- Germany
- Prior art keywords
- group
- formula
- optionally substituted
- groups
- compounds
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims description 21
- 230000008569 process Effects 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 6
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 title abstract description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 title abstract description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title abstract description 3
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 125000003118 aryl group Chemical group 0.000 claims abstract description 20
- -1 sulpho Chemical class 0.000 claims abstract description 13
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 125000002252 acyl group Chemical group 0.000 claims abstract description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 125000005110 aryl thio group Chemical group 0.000 claims abstract description 5
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 5
- 150000001602 bicycloalkyls Chemical group 0.000 claims abstract description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 5
- 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 claims abstract description 3
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims abstract description 3
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- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims abstract description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims abstract description 3
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- 125000000168 pyrrolyl group Chemical group 0.000 claims abstract description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims abstract description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims abstract description 3
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 14
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- 239000007858 starting material Substances 0.000 claims description 8
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- 125000003277 amino group Chemical group 0.000 claims description 5
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- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
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- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
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- LOGFVTREOLYCPF-KXNHARMFSA-N (2s,3r)-2-[[(2r)-1-[(2s)-2,6-diaminohexanoyl]pyrrolidine-2-carbonyl]amino]-3-hydroxybutanoic acid Chemical compound C[C@@H](O)[C@@H](C(O)=O)NC(=O)[C@H]1CCCN1C(=O)[C@@H](N)CCCCN LOGFVTREOLYCPF-KXNHARMFSA-N 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- NZXOMRVNSPIUFN-UHFFFAOYSA-N 2-[(2,6-dimethoxyphenoxy)methyl]-6-(4-fluorophenyl)-5-imidazol-1-yl-1h-benzimidazole Chemical compound COC1=CC=CC(OC)=C1OCC1=NC2=CC(N3C=NC=C3)=C(C=3C=CC(F)=CC=3)C=C2N1 NZXOMRVNSPIUFN-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 2
- 125000005002 aryl methyl group Chemical group 0.000 claims description 2
- 150000001805 chlorine compounds Chemical class 0.000 claims description 2
- HORJYIAQYXUVQZ-UHFFFAOYSA-N n-[(6-imidazol-1-yl-1h-benzimidazol-2-yl)methyl]benzenesulfonamide;dihydrochloride Chemical compound Cl.Cl.C=1C=CC=CC=1S(=O)(=O)NCC(NC1=C2)=NC1=CC=C2N1C=CN=C1 HORJYIAQYXUVQZ-UHFFFAOYSA-N 0.000 claims description 2
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- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
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- HCCZCHZZERCDRY-UHFFFAOYSA-N 2-[(2,6-dimethoxyphenoxy)methyl]-6-imidazol-1-yl-1h-benzimidazole;dihydrochloride Chemical compound Cl.Cl.COC1=CC=CC(OC)=C1OCC1=NC2=CC=C(N3C=NC=C3)C=C2N1 HCCZCHZZERCDRY-UHFFFAOYSA-N 0.000 claims 1
- LAANOCDIBMWUOO-UHFFFAOYSA-N 2-[(2,6-dimethylphenyl)sulfanylmethyl]-6-imidazol-1-yl-1h-benzimidazole;dihydrochloride Chemical compound Cl.Cl.CC1=CC=CC(C)=C1SCC1=NC2=CC=C(N3C=NC=C3)C=C2N1 LAANOCDIBMWUOO-UHFFFAOYSA-N 0.000 claims 1
- YKDRETAFGDVXHL-UHFFFAOYSA-N 6-imidazol-1-yl-2-(phenoxymethyl)-1h-benzimidazole Chemical compound N=1C2=CC=C(N3C=NC=C3)C=C2NC=1COC1=CC=CC=C1 YKDRETAFGDVXHL-UHFFFAOYSA-N 0.000 claims 1
- MSVODBIFFZTVFF-UHFFFAOYSA-N 6-imidazol-1-yl-2-(phenylsulfanylmethyl)-1h-benzimidazole Chemical compound N=1C2=CC=C(N3C=NC=C3)C=C2NC=1CSC1=CC=CC=C1 MSVODBIFFZTVFF-UHFFFAOYSA-N 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract description 2
- 125000005208 trialkylammonium group Chemical group 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000001769 aryl amino group Chemical group 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 238000004458 analytical method Methods 0.000 description 47
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- 230000008018 melting Effects 0.000 description 16
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- RZVSEOHTMNBSRH-UHFFFAOYSA-N n-[[5-imidazol-1-yl-6-(4-pyridin-4-ylphenyl)-1h-benzimidazol-2-yl]methyl]-2,6-dimethoxy-n-methylaniline Chemical compound COC1=CC=CC(OC)=C1N(C)CC1=NC2=CC(N3C=NC=C3)=C(C=3C=CC(=CC=3)C=3C=CN=CC=3)C=C2N1 RZVSEOHTMNBSRH-UHFFFAOYSA-N 0.000 description 1
- YFRFVOIPDGBXED-UHFFFAOYSA-N n-[[5-imidazol-1-yl-6-(4-pyridin-4-ylphenyl)-1h-benzimidazol-2-yl]methyl]-2,6-dimethoxyaniline Chemical compound COC1=CC=CC(OC)=C1NCC1=NC2=CC(C=3C=CC(=CC=3)C=3C=CN=CC=3)=C(N3C=NC=C3)C=C2N1 YFRFVOIPDGBXED-UHFFFAOYSA-N 0.000 description 1
- JBABDLXGLRBXQU-UHFFFAOYSA-N n-[[6-(4-fluorophenyl)-5-imidazol-1-yl-1h-benzimidazol-2-yl]methyl]-2,6-dimethoxy-n-methylaniline Chemical compound COC1=CC=CC(OC)=C1N(C)CC1=NC2=CC(N3C=NC=C3)=C(C=3C=CC(F)=CC=3)C=C2N1 JBABDLXGLRBXQU-UHFFFAOYSA-N 0.000 description 1
- GRMPMJXGPPEGSZ-UHFFFAOYSA-N n-[[6-(4-fluorophenyl)-5-imidazol-1-yl-1h-benzimidazol-2-yl]methyl]-2,6-dimethoxyaniline Chemical compound COC1=CC=CC(OC)=C1NCC1=NC2=CC(N3C=NC=C3)=C(C=3C=CC(F)=CC=3)C=C2N1 GRMPMJXGPPEGSZ-UHFFFAOYSA-N 0.000 description 1
- WABYAFPSBJLQQX-UHFFFAOYSA-N n-hydroxy-4-[(6-imidazol-1-yl-1h-benzimidazol-2-yl)methoxy]benzamide Chemical compound C1=CC(C(=O)NO)=CC=C1OCC1=NC2=CC=C(N3C=NC=C3)C=C2N1 WABYAFPSBJLQQX-UHFFFAOYSA-N 0.000 description 1
- UPSJGCORLWBKKJ-UHFFFAOYSA-N n-hydroxy-4-[(6-imidazol-1-yl-1h-benzimidazol-2-yl)methylcarbamoylamino]benzamide Chemical compound C1=CC(C(=O)NO)=CC=C1NC(=O)NCC1=NC2=CC=C(N3C=NC=C3)C=C2N1 UPSJGCORLWBKKJ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000000770 proinflammatory effect Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9709710A FR2766822B1 (fr) | 1997-07-30 | 1997-07-30 | Nouveaux derives de benzimidazole, de benzoxazole et de benzothiazole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69800882D1 DE69800882D1 (de) | 2001-07-12 |
| DE69800882T2 true DE69800882T2 (de) | 2002-03-28 |
Family
ID=9509817
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69800882T Expired - Fee Related DE69800882T2 (de) | 1997-07-30 | 1998-07-28 | Benzimidazol-, Benzoxazol-, und Benzothiazolderivate, Verfahren zu ihrer Herstellung und pharmazeutische Zusammensetzungen die sie enthalten |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US6040327A (xx) |
| EP (1) | EP0894795B1 (xx) |
| JP (1) | JPH11100368A (xx) |
| CN (1) | CN1087740C (xx) |
| AT (1) | ATE201868T1 (xx) |
| AU (1) | AU734447B2 (xx) |
| BR (1) | BR9802804A (xx) |
| CA (1) | CA2244438A1 (xx) |
| DE (1) | DE69800882T2 (xx) |
| DK (1) | DK0894795T3 (xx) |
| ES (1) | ES2159922T3 (xx) |
| FR (1) | FR2766822B1 (xx) |
| GR (1) | GR3036473T3 (xx) |
| HK (1) | HK1018440A1 (xx) |
| HU (1) | HUP9801725A1 (xx) |
| NO (1) | NO983493L (xx) |
| NZ (1) | NZ331153A (xx) |
| PL (1) | PL327748A1 (xx) |
| PT (1) | PT894795E (xx) |
| ZA (1) | ZA986814B (xx) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6248770B1 (en) * | 1998-07-09 | 2001-06-19 | Boehringer Ingelheim Pharma Kg | Benzimidazoles having antithrombotic activity |
| US6808902B1 (en) | 1999-11-12 | 2004-10-26 | Amgen Inc. | Process for correction of a disulfide misfold in IL-1Ra Fc fusion molecules |
| TWI225488B (en) * | 1999-12-21 | 2004-12-21 | Janssen Pharmaceutica Nv | Derivatives of homopiperidinyl substituted benzimidazole analogues |
| US6451832B2 (en) | 1999-12-23 | 2002-09-17 | Boehringer Ingelheim Pharma Kg | Benzimidazoles with antithrombotic activity |
| US6660858B2 (en) | 2001-03-28 | 2003-12-09 | Lion Bioscience Ag | 2-aminobenzoxazole derivatives and combinatorial libraries thereof |
| DK2295081T3 (en) | 2001-06-26 | 2019-02-18 | Amgen Inc | Antibodies to OPGL |
| AU2002316384A1 (en) * | 2001-06-26 | 2003-03-03 | Photomed Technologies, Inc. | Multiple wavelength illuminator |
| AU2003207808A1 (en) * | 2002-02-21 | 2003-09-09 | Eli Lilly And Company | Peroxisome proliferator activated receptor modulators |
| WO2004060911A2 (en) * | 2002-12-30 | 2004-07-22 | Amgen Inc. | Combination therapy with co-stimulatory factors |
| US7863310B2 (en) * | 2004-02-03 | 2011-01-04 | Eli Lilly And Company | Kinase inhibitors |
| PE20070335A1 (es) * | 2005-08-30 | 2007-04-21 | Novartis Ag | Benzimidazoles sustituidos y metodos para su preparacion |
| KR101047221B1 (ko) * | 2005-09-02 | 2011-07-06 | 에프. 호프만-라 로슈 아게 | 벤조옥사졸, 옥사졸로피리딘, 벤조싸이아졸 및싸이아졸로피리딘 유도체 |
| ES2551709T3 (es) * | 2006-12-15 | 2015-11-23 | Janssen Pharmaceutica, N.V. | Inhibidores Bencimidazola TRPV1 |
| TWI443090B (zh) * | 2007-05-25 | 2014-07-01 | Abbvie Deutschland | 作為代謝性麩胺酸受體２（ｍｇｌｕ２ 受體）之正向調節劑之雜環化合物 |
| WO2009079008A1 (en) * | 2007-12-19 | 2009-06-25 | Yangbo Feng | Benzopyrans and analogs as rho kinase inhibitors |
| JP2011507851A (ja) * | 2007-12-19 | 2011-03-10 | ザ スクリプス リサーチ インスティチュート | Ｒｈｏキナーゼインヒビターとしてのベンゾイミダゾールおよびアナログ |
| MX2011004505A (es) * | 2008-10-29 | 2011-05-31 | Merck Sharp & Dohme | Derivados novedosos de bencimidazol ciclico, utiles como agentes antidiabeticos. |
| EP2951170B1 (en) | 2013-02-04 | 2018-10-24 | Janssen Pharmaceutica NV | Flap modulators |
| TWI644899B (zh) | 2013-02-04 | 2018-12-21 | 健生藥品公司 | Ｆｌａｐ調節劑 |
| NZ739676A (en) * | 2015-09-18 | 2022-02-25 | Merck Patent Gmbh | Heteroaryl compounds as irak inhibitors and uses thereof |
| WO2020035482A1 (en) | 2018-08-13 | 2020-02-20 | Iltoo Pharma | Combination of interleukin-2 with an interleukin 1 inhibitor, conjugates and therapeutic uses thereof |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE465803A (xx) * | 1944-01-22 | |||
| US3182070A (en) * | 1962-05-24 | 1965-05-04 | Dow Chemical Co | Benzimidazole compounds |
| FR1450560A (fr) * | 1965-05-26 | 1966-06-24 | Chimetron Sarl | Nouveaux benzimidazoles possédant deux substituants hétérocycliques |
| DE3039208A1 (de) * | 1980-10-17 | 1982-05-13 | Basf Ag, 6700 Ludwigshafen | Neue sulfone, deren herstellung und verwendung |
| CA1279648C (en) * | 1986-07-11 | 1991-01-29 | Haruo Kuriyama | 2-(4-pyridylaminometyl)-benzimidazole derivatives having antiviral activity |
| DE3819823A1 (de) * | 1988-06-08 | 1989-12-21 | Schering Ag | Durch zum teil kondensierte heterocyclen substituierte indole, indazole und benzimidazole, verfahren zu ihrer herstellung und ihre verwendung als mittel mit herbizider wirkung |
| JP2869561B2 (ja) * | 1989-05-22 | 1999-03-10 | 大塚製薬株式会社 | 血小板粘着抑制剤 |
| JPH03232868A (ja) * | 1990-02-05 | 1991-10-16 | Nippon Telegr & Teleph Corp <Ntt> | 新規光学活性化合物及び液晶組成物 |
| US5612360A (en) * | 1992-06-03 | 1997-03-18 | Eli Lilly And Company | Angiotensin II antagonists |
| US6815461B1 (en) * | 1994-01-20 | 2004-11-09 | The University Of North Carolina At Chapel Hill | Method of inhibiting retroviral integrase |
| US5552426A (en) * | 1994-04-29 | 1996-09-03 | Eli Lilly And Company | Methods for treating a physiological disorder associated with β-amyloid peptide |
| EP0785927B1 (en) * | 1994-10-12 | 2003-08-27 | Euroceltique S.A. | Novel benzoxazoles |
| AU3461697A (en) * | 1996-07-19 | 1998-02-10 | Takeda Chemical Industries Ltd. | Heterocyclic compounds, their production and use |
| FR2751649B1 (fr) * | 1996-07-26 | 1998-08-28 | Adir | Nouveaux derives de benzimidazole, de benzoxazole et de benzothiazole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
-
1997
- 1997-07-30 FR FR9709710A patent/FR2766822B1/fr not_active Expired - Fee Related
-
1998
- 1998-07-22 US US09/120,487 patent/US6040327A/en not_active Expired - Fee Related
- 1998-07-27 JP JP10210640A patent/JPH11100368A/ja active Pending
- 1998-07-28 EP EP98401920A patent/EP0894795B1/fr not_active Expired - Lifetime
- 1998-07-28 DK DK98401920T patent/DK0894795T3/da active
- 1998-07-28 AT AT98401920T patent/ATE201868T1/de not_active IP Right Cessation
- 1998-07-28 DE DE69800882T patent/DE69800882T2/de not_active Expired - Fee Related
- 1998-07-28 PT PT98401920T patent/PT894795E/pt unknown
- 1998-07-28 ES ES98401920T patent/ES2159922T3/es not_active Expired - Lifetime
- 1998-07-29 NO NO983493A patent/NO983493L/no not_active Application Discontinuation
- 1998-07-29 PL PL98327748A patent/PL327748A1/xx not_active Application Discontinuation
- 1998-07-29 CA CA002244438A patent/CA2244438A1/fr not_active Abandoned
- 1998-07-29 NZ NZ331153A patent/NZ331153A/xx unknown
- 1998-07-29 CN CN98117575A patent/CN1087740C/zh not_active Expired - Fee Related
- 1998-07-30 AU AU78608/98A patent/AU734447B2/en not_active Ceased
- 1998-07-30 HU HU9801725A patent/HUP9801725A1/hu unknown
- 1998-07-30 BR BR9802804-9A patent/BR9802804A/pt not_active IP Right Cessation
- 1998-07-30 ZA ZA986814A patent/ZA986814B/xx unknown
-
1999
- 1999-08-05 HK HK99103381A patent/HK1018440A1/xx not_active IP Right Cessation
-
2001
- 2001-08-30 GR GR20010401332T patent/GR3036473T3/el not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| HU9801725D0 (en) | 1998-09-28 |
| BR9802804A (pt) | 2000-05-02 |
| AU7860898A (en) | 1999-02-11 |
| ZA986814B (en) | 1999-02-02 |
| NO983493L (no) | 1999-02-01 |
| EP0894795A1 (fr) | 1999-02-03 |
| CN1087740C (zh) | 2002-07-17 |
| JPH11100368A (ja) | 1999-04-13 |
| DK0894795T3 (da) | 2001-09-03 |
| US6040327A (en) | 2000-03-21 |
| EP0894795B1 (fr) | 2001-06-06 |
| ES2159922T3 (es) | 2001-10-16 |
| NO983493D0 (no) | 1998-07-29 |
| FR2766822B1 (fr) | 2001-02-23 |
| CN1210859A (zh) | 1999-03-17 |
| DE69800882D1 (de) | 2001-07-12 |
| CA2244438A1 (fr) | 1999-01-30 |
| AU734447B2 (en) | 2001-06-14 |
| FR2766822A1 (fr) | 1999-02-05 |
| HK1018440A1 (en) | 1999-12-24 |
| ATE201868T1 (de) | 2001-06-15 |
| NZ331153A (en) | 1999-07-29 |
| PT894795E (pt) | 2001-09-28 |
| PL327748A1 (en) | 1999-02-01 |
| GR3036473T3 (en) | 2001-11-30 |
| HUP9801725A1 (hu) | 2000-11-28 |
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